A Couple of Comments
I can't answer all of your questions, but I do have some suggestions:1. Install a mast plate under the foot of your mast. This is a bracket that has mounting holes for your halyard blocks and is preferable to drilling holes in your mast or deck for pad eyes.2. Invest in quality, ball bearing turning blocks at the get-go (I have to replace some of mine where I skimped). If you don't, you'll be disappointed with all of the friction that will build up. 3. Garhauer is a good source for hardware. They supply what Catalina uses on new boats and will know which items to use for each purpose, including all of the blocks and rope clutches, etc. When choosing your multi-sheave turning blocks (aka deck organizers) for your deck, think about getting ones with one more sheave than you need if possible. If you need 2 or 3 sheaves, buy one with 3 or 4. That will give you flexibility for the future for a moderate increase in cost. 4. Try to minimize the acuteness of your angles (minimizes friction).5. I wouldn't rely on others' measurements, do your own. Your layout may vary and you may prefer longer or shorter tails. The easiest way to do this is to work from your existing halyards. You can tie a line onto the end and run it back to the cockpit, thereby estimating how much additional length you'll need. When the sails are down, you'll want enough of a tail to wrap around your winch and still have a good 4'- 5' or so to grab onto.6. Get rid of the topping lift and install a rigid boom vang while you're at it. You'll eliminate one line this way (again, Garhauer). Use the money you'll save on additional hardware to contribute toward the cost of the rigid vang.7. For securing the lines in the cockpit, you'll use a combination of rope clutches, cam cleats and/or jam cleats. Some of this is a matter of preference, but I'd definitely use rope clutches for the halyards themselves.8. I had to modify the teak risers for my mainsheet traveler by cutting a "tunnel" into their bases to be able to run the halyards underneath the risers. This was preferable to drilling holes and isn't too difficult.9. Check out some newer C30's to get an idea on placement, but understand that you probably won't be able to duplicate it perfectly. If your experience is anything like mine (1981 C30, standard rig), you'll be a little disappointed as to how difficult and slow it is to raise the sails compared to working at the base of the mast. This is all due to friction. I've left my mast winches in place and they've been a lifesaver when I needed to move fast.I've included a link to Garhauer and, no, I don't work for them, I just like their stuff and their prices.